


Wingman

by Lif61 (UltimateFandomTrash)



Category: Supernatural
Genre: Bisexual Dean Winchester, Comedy, Crack, Getting Together, I hope at least some of this is funny, Implied/Referenced Homophobia, M/M, Sassy Castiel (Supernatural)
Language: English
Status: Completed
Published: 2019-09-11
Updated: 2019-09-11
Packaged: 2020-10-14 10:14:14
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,720
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/20599073
Author URL: https://archiveofourown.org/users/UltimateFandomTrash/pseuds/Lif61
Summary: Dean bails on research for a case, and Castiel goes with him, saying he can be his wingman for the night. Things aren't going so well, and it seems as if Cas has an ulterior motive.





	Wingman

**Author's Note:**

> Wrote this based on a tumblr post I saw that talked about how it's good Sam and Dean are good-looking because they actually have some pretty creepy truths about them. Thought it be funny to see Dean trying to pick some women up, lying and flirting his way to their hearts, and Castiel just ends up being blunt and honest. And of course, I couldn't do it without making it into Destiel.
> 
> The joke Dean tells Cas is based on another tumblr post I saw. I just changed it to make it more appropriate to Dean's life. Hopefully you can guess what it is based on Dean and Cas' conversation.

Sam was stuck in a motel room doing research on the history of the current crappy town they were staying in. Yet another dot on the map of the never-ending road trip that was their lives. Dean had bailed and was heading out to a bar. Castiel had insisted on coming, which was odd, to say the least. Castiel couldn’t get drunk, he wasn’t great with women, or even men, he didn’t eat, probably didn’t know what pool was, would think a game of darts was someone trying to attack him, and he looked like he had a stick up his ass.

“Cas, you sure about this?” Dean asked once he parked the Impala outside the bar. 

It was night, and he could see through the window at the various patrons, the women looking for hookups, the men drowning their sorrows, the various groups of people just trying to get away from life for a bit, and the flashing lights practically saying  _ COME ON IN! _ It was Dean’s kind of place, but Cas’? No.

“Yes,” Castiel answered, frowning, and then looking over at him. “I can be your wingman.”

“An angel being my wingman, huh?”

Castiel nods, eyes big, sure of himself.

“Alright, well, let’s go get some.”

Dean doesn’t know if that’s actually what he wants that night. If anything, he’d kept looking at Cas while driving, passing it off as having to check his mirrors, or see if he could merge right, or make a turn. But then he’d done it when they were the only ones on the road, and he’d kept doing it, right until they’d almost gone off it and hit a tree. Cas hadn’t even noticed, seeming deep in his thoughts.

So yeah, Dean was distracted. But he needed an excuse to be at a bar, needed to stay away from those crappy books Sam had dug out of the  _ ancient _ basement in the library, and hell, girls were pretty.

Cas licked his lips.

Fuck, they didn’t have lips like those though.

They headed into the bar, and Dean ordered a drink. If he was on his own, usually he’d hustle pool, or play up the sad, lonely look, but since he was with Cas, he turned on his good sense of humor.

Castiel didn’t get his jokes.

“Come on, buddy, you’re supposed to laugh at this stuff,” he hissed, leaning in.

Castiel struck a blow, saying, “Why would I laugh if they’re not funny?”

“Dude, everyone laughs at the hunter and a vampire walk into a bar joke.”

“Why would a vampire leave if a hunter’s insulted?”

“No, no, Cas, that’s not— The blood. The vampire thinks they’re not serving—“

Cas was smiling now, looking up, having come to his own conclusions.

“Oh, I get it. He leaves to go kill the hunter and drink his blood. It’s funny because the vampire went into a place where drinks are served to get himself a drink.”

Cas winked.

Dean hung his head, face in one hand. He was sure Cas’ eyes were sparkling.

“Cas, no.”

“Then I don’t get it.”

Dean got up from his stool, and pat him on the shoulder. “No, you really don’t.”

There was a woman, maybe in her early thirties, standing by a table eyeing the pool table over near the back, and Dean nodded at her, smiling as he walked over. She smiled back, moving her hair behind her ear, shifting her legs a bit, stirring her straw in her drink. Alright, she was interested. A man had been talking to her, but he’d just walked away, and it seemed as if she’d told him to leave. He was now grumbling about it to some other guy with a hat and a bottle of beer.

Dean had taken his beer with him, and he tilted his head to see if Cas was coming. The angel downed a shot, seeming disgruntled, and then he was on his way.

“Why, hello there,” Dean greeted, setting his beer down. “So, no luck with that guy?” he asked, gesturing off to the offending person of conversation.

She frowned a bit, shaking her head, and the glitter in her eyeshadow caught the light. She was pretty; round face, tan skin, curly hair, dressed just the right way to make him interested too: jeans, and an AC/DC tank top.

“He thought dick jokes were appropriate five minutes into the relationship.”

Dean winced, catching Cas’ eye as he came over, and then looked back to the woman. “Ah, that’s not good. Well, I’m Dean.” Cas was at his side now. “This here is Cas.”

“Nice to meet you boys. I’m Sara.”

The three of them ended up talking, but if Dean was being honest, Cas ended up listening more, and piping up at random times, making things a bit awkward.

Then they got on the topic of what Dean did for a living.

“Oh, I, uh… do jobs here and there. Trade work mostly,” Dean lied. “Like to work on cars, but I also like staying on the road.”

“So, what, are you a traveling mechanic?”

“Something like that. I—”

“He’s lying,” Cas butt in. “He doesn’t have a job.”

Dean turned, staring at his friend, completely shocked, hand tightening around his beer, mouth agape. “I-I…” An uncomfortable, nervous smile came upon his face. “No, no, he’s drunk, had a bit too much to drink. Cas, why don’t you go head back, yeah?”

“I don’t get drunk. Ever.”

“He’s lying. I have a job.”

“No, Dean. You don’t get paid.”

Sara was looking at both of them, face scrunched up as if she was disgusted, or creeped out.

“What is this?”

“A joke is what this is, right, Cas?” Dean asked his friend, a dangerous tone to his voice. There was a gun in the waistband of his pants, and Cas knew it. He wanted him to think he’d use it if this went south.

“No, I’m sorry.”

Castiel strode away, coat swishing about him, Dean did his best to smile at Sara, but she hurriedly gathered her purse, and left as quickly as she could.

So Dean tried with another woman. That didn’t go so well…

“You live around here? I haven’t seen you in town.”

“Yeah, outskirts of town. Just moved recently. Tryin’ to get to know the place.”

“He’s staying in a motel room with his brother. They always share.”

“Why don’t you come back to my place for a bit?”

“If you ask him if he has a gun in his pocket or if he’s just pleased to see you… he has a gun.”

“Who’s your friend?”

“Oh, this guy? Handsome, right? He’s my partner, working a case with him. Met him back in 2008 during—”

“He stabbed me.”

Dean drew Castiel aside near the bathrooms. It was late and the bar had started clearing out, and there was a distinct lack of women since Castiel had been scaring them all away, and Dean wasn’t looking for guys that night, not since he had Cas, but he was going to start in on them.

“What’s your problem?”

“I’m being your wingman,” Castiel answered, monotone, looking at him, but not in his eyes, just beneath them.

The bathroom door swung open, a burly man stepping out, and Dean grabbed Cas, shoving him inside. He locked the door behind them.

The bathroom was as gross as he’d expected, and tagged with graffiti. God, he was so embarrassed from this night he just wanted to leave out the damn window. Hell, it looked like he and Cas could both fit.

“No, you’re  _ sucking _ at being my wingman,” he told him.

Castiel looked to the side, and he wrinkled his nose.

“Humans are so… odd. You consume and consume, and yet you need rooms like these.”

“Yeah, Cas, not really the point.”

“But then you have nights like this one, looking for release.”

“Okay, and? Cut to the chase. I hate cliffhangers.”

“I wasn’t being your wingman.”

“Good, kinda figured that out myself. What the hell were you doing?”

There was banging on the door, and a voice came through, saying something insulting. Clearly the man outside could hear two voices in there. No way in hell was Dean going back out through the front entrance.

He and Cas both turned to the door.

“Guess it’s time to go. Alright, we get out through the window, circle back around to the Impala.”

“Dean, it’s not a monster.”

“Yeah, but that human sound friendly to you?”

“The words he’s saying, what do they mean?”

“Nothing you’d hear at your grandma’s. Come on.”

It hurt hearing them, but he’d gotten it from time to time, and as long as it wasn’t hurting Cas, he was good.

He went over to the other side of the room and started opening the window, and climbed through, landing in a pile of shrubs.

Cas came out next, and then they went to the parking lot. Dean was mad at him, but he held onto his forearm.

It was quiet for a bit once they were back on the road, and finally, Dean asked, “You didn’t want me to get with anyone tonight, did you?”

“I… I did.”

“You?”

“Yeah.”

“Alright, well, I got a pretty good mixed tape in the glove compartment, found some nice little spot out in the country earlier today, and there’s a blanket in the trunk, and wide open sky just for us.”

Castiel wasn’t breathing. Dean was sure of it.

“Cas. Cas, you good?”

He glanced over at him, and the angel was just smiling at him, but also seemed to be in a state of shock.

“I didn’t think it’d be so easy.”

“It wasn’t. You embarrassed me all night,” Dean chided, switching the stereo on as he drove. It was a bit of a long drive to the place he wanted to go to. “Come on, who’d you talk to about that? You can’t come up with that stuff on your own.”

“Sam.”

“Ugh, fuck Sam. He’s gonna be in trouble tomorrow.”

“But you actually want this?” Cas questioned.

Dean wasn’t taking a turn, wasn’t making any excuse, and took a good look at Castiel anyway, saw his eyes reflect the light from a streetlamp.

“You bet your ass I do, wingman.”


End file.
